2-[3,6-bis(acetyloxy)-2,7-dichloro-9H-xanthen-9-yl]benzoic acid

• ChemBase ID: 155222
• Molecular Formular: C24H16Cl2O7
• Molecular Mass: 487.28564
• Monoisotopic Mass: 486.02730821
• SMILES: CC(=O)Oc1cc2c(cc1Cl)C(c1cc(c(cc1O2)OC(=O)C)Cl)c1ccccc1C(=O)O
• Canonical SMILES: CC(=O)Oc1cc2Oc3cc(OC(=O)C)c(cc3C(c2cc1Cl)c1ccccc1C(=O)O)Cl
• InChI: InChI=1S/C24H16Cl2O7/c1-11(27)31-21-9-19-15(7-17(21)25)23(13-5-3-4-6-14(13)24(29)30)16-8-18(26)22(32-12(2)28)10-20(16)33-19/h3-10,23H,1-2H3,(H,29,30)
• InChIKey: PXEZTIWVRVSYOK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[3,6-bis(acetyloxy)-2,7-dichloro-9H-xanthen-9-yl]benzoic acid
• IUPAC Traditional name: 2-[3,6-bis(acetyloxy)-2,7-dichloro-9H-xanthen-9-yl]benzoic acid
• Synonyms: 2′,7′-Dichlorodihydrofluorescein diacetate; 2′,7′-Dichlorofluorescin diacetate; 2-[3,6-Bis(acetyloxy)-2,7-dichloro-9H-xanthen-9-yl]benzoic Acid; o-(2,7-Dichloro-3,6-dihydroxyxanthen-9-yl)benzoic Acid Diacetate; 2',7'-Dichlorodihydrofluorescein Diacetate; DCFH; H2DCFDA; 2',7'-Dichlorodihydrofluorescein Diacetate

Database IDs

• CAS Number: 4091-99-0
• MDL Number: MFCD00128955
• Beilstein Number: 4610273
• PubChem SID: 162249360; 24894058
• PubChem CID: 77718

CALCULATED PROPERTIES

• Acid pKa: 3.886385
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.4742775
• LogD (pH = 7.4): 1.8725264
• Log P: 5.0930986
• Molar Refractivity: 119.7522 cm^3
• Polarizability: 46.35783 Å^3
• Polar Surface Area: 99.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97%
• Empirical Formula (Hill Notation): C24H16Cl2O7

DETAILS

Sigma Aldrich - D6883

Frequently Asked Questions
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Application
A cell-permeable non-fluorescent probe. It is de-esterified intracellularly and turns to highly fluorescent 2′,7′-dichlorofluorescein upon oxidation.Applications: sensitive and rapid quantitation of oxygen-reactive species in response to oxidative metabolism; microplate assay for detecting oxidative products in phagocytic cells, and quantitative multiwell myeloid differentiation assay.

Toronto Research Chemicals - D434215

2',7'-Dichlorodihydrofluorescein as a cell-permeable non-fluorescent probe. It is de-esterified intracellularly and turns to highly fluorescent 2′,7′-dichlorofluorescein upon oxidation.

REFERENCES

• Lebel, C., et al.: Chem. Res. Toxicol., 5, 227 (1992)
• Kjaer, M., et al.: Lipids, 43, 813 (1992)
• Baron, C., et al.: J. Agric. Food Chem., 57, 4185 (1992)